Carlie Statsky
Field Guide · First Edition

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First Edition · 2026
Field Guide to AI for the Wedding Creative
a notebook of 24
working prompts
By Carlie Statsky
Contents

what’s inside

A Note Before We Begin

why this guide exists

I’ve spent the last year working with most of the major AI tools — ChatGPT, Gemini, Copilot, Perplexity, Grok, and Claude. I tried them on real things: contracts I needed reviewed, pricing questions I’d been avoiding, Instagram captions that needed to sound like me, client emails I couldn’t quite get the tone right on. I wasn’t curious in the abstract. As a mom of two with a business to run, I was looking for something that would save me time and increase my profits without losing my voice or vision.

For the work that matters most in this field — strategic thinking, business planning, contracts, and writing that has to sound like me — Claude is the one I kept coming back to. The reasoning was sharper. The writing felt closer to mine. It pushed back when I was wrong instead of agreeing reflexively. That’s not brand loyalty; it’s just what happened after a year of comparing.

What follows are the prompts and workflows I’ve actually used in my own business. None of this is theory. Almost all of it has been tested on real weddings, real clients, real days I needed to make the math work. A few are still on my own to-do list — the blog post prompt is the obvious tell, considering I haven’t written one in far too many years (and yes, I’m fully aware of the irony). They’re still in the guide because the prompt itself is sound, and because I’d rather give you the full set than only what I’ve perfectly executed myself.

This is not a guide about replacing your voice or your judgment. It’s about offloading the parts of your work that don’t need either — so the parts that do can have more of you in them.

A note before you begin: AI is a tool, and like any tool, the work it produces reflects the care taken with it. Tell it to be honest. Tell it not to invent. Tell it to flag anything that could land carelessly. We are still the ones serving real people on real days, and that responsibility doesn’t scale — only the work around it does.

One more thing. Don’t try to do this all at once. There are 24 prompts in here, and if you sat down to run all of them this weekend you’d lose momentum before you got anywhere. Pick the one entry you think would be most useful to you right now — just one — and start there.

This is not a static PDF. It is a working document — built so you can jump to any section from the contents, copy any prompt with one tap, and use it the way you actually use the rest of your tools.

If something here saves you a single afternoon, or books you a single wedding at a higher rate, it’s done its job.

Part One

brand & website

the work that decides whether the right clients ever email you in the first place
No. 01

an honest read on your website with a luxury client in mind

Luxury clients don’t evaluate your website the way you do. They land on the homepage and react emotionally to your imagery within a few seconds — before they read a single word. Then they scan your copy, your investment page, your about. They decide in about ninety seconds whether you feel like the right fit. The imagery has to do the first piece of work; the copy carries the second. Most of us audit one and not the other.

Prompt
I’m a [your role] in [region], and I want to attract couples with a $250K+ budget for a Northern California wedding. Please open [yoursite.com] and walk through every page in the order a first-time visitor would experience it. For each page, evaluate two things separately: (1) the imagery — what emotional response does the first image and the overall image curation create, where does the visual story drift or weaken, which images undersell the caliber of work or feel inconsistent in style/color/mood, and which specific images should be swapped or removed; (2) the copy — what’s working, what undersells me or reads as small/scarce, what’s missing that this caliber of client would expect to see, and one specific change to fix it. At the end: the three highest-impact changes I should make first across both imagery and copy, ranked by booking impact, with one sentence on why each one matters most for the client I’m describing. Be candid, not flattering.
No. 02

a brand voice document, drawn from what you’ve already written

The reason AI writing sounds like AI is that most people skip this step. Build a voice document once and paste it into every future prompt. Your captions, emails, and blog posts will start sounding like you again.

Prompt
I want to build a brand voice document I can paste into every future writing prompt so my AI-assisted writing actually sounds like me. Here are 8–10 pieces of writing I’m proud of — captions, blog posts, client emails: [paste them]. Analyze them and produce a one-page voice document with these sections: (1) sentence rhythm and cadence — how long, how varied, where I break rules; (2) vocabulary — specific words I reach for and words I avoid; (3) emotional register — warm, dry, observational, something else; (4) structural habits — how I open, how I close, how I transition; (5) three contrast samples of writing that does NOT sound like me, so I know what to flag and reject in future AI drafts. Format it as a document I can paste at the top of every future prompt.
No. 03

a read on your instagram from outside your own head

You’ve been staring at your own grid too long to see it. Ask for a fresh pair of eyes — someone who has seen thousands of accounts in your industry.

Prompt
Please open [@yourhandle] on Instagram and review my last 30 posts as if you were a potential client landing on my profile for the first time. Context: I’m a [role] in [region], my ideal client is [describe in one sentence], and my specific goal right now is [e.g., booking $15K+ weddings, or attracting more editorial work]. Tell me, in this order: (1) the story this grid actually tells in one paragraph — not what I want it to tell; (2) the kind of client it speaks to right now, and what they’d care about; (3) the three biggest inconsistencies hurting bookings — visual, tonal, or strategic; (4) the three highest-impact changes I should make in the next 30 days, ranked by effort vs. payoff. Be candid. Skip flattery. I can take it.Note: AI tools can browse public Instagram profiles but cannot see private accounts or your analytics. Pair this with a screenshot of your insights for a sharper read.
No. 04

caption help that doesn’t sound like AI

Default AI captions are overwritten and over-emoted. The trick is to feed it your voice document (entry 02) and a few specific samples before each prompt.

Prompt
I need three Instagram caption options for [describe the post in one sentence, or paste the photo]. First, study my voice using: [paste your brand voice document from entry 02]. Five recent captions I’m proud of: [paste them]. Now write three options at different lengths: one short (under 15 words), one medium (40–60 words), one longer (100–130 words with a real story). Strict rules: match my voice exactly, no emoji unless I use them in the samples, no “swipe to see more” or “link in bio,” no questions at the end unless they’re genuinely interesting, no AI-rhythm sentences (lists of three, neat parallel structures). If any option starts to feel generic, rewrite it before showing me.
Part Two

marketing & visibility

the slower work of being seen by the right people
No. 05

a 12-month marketing plan built from where you already are

Most marketing plans fail because they’re written in a vacuum. The good ones start from where you already are. AI can synthesize your site, your social, and your stated goals into something coherent.

Prompt
Please review my website [yoursite.com] and Instagram [@yourhandle], then draft a 12-month marketing plan for my business. My specific goals: [list them with numbers where possible — e.g., book 15 weddings at $X average, increase Bay Area inquiries by Y%, get published in two specific outlets]. My constraints: [hours per week I can give to marketing, any budget, what I won’t do]. Structure the plan as: (1) four quarterly themes that build on each other; (2) a monthly content focus for each quarter, with specific deliverables; (3) the three platforms I should prioritize and exactly why, based on what I’m already doing well; (4) the platforms I should stop spending time on, with reasoning; (5) a ranked list of 10–15 specific publications, podcasts, planners, or venues to pursue this year, with a one-line note on why each fits. Reference what you actually saw on my site and feed — skip generic advice.
No. 06

match your strengths to the couple’s stated needs before the call

Most discovery calls are spent improvising. The ones that book are the ones where you walk in already knowing which parts of your work matter most to this couple — and how to talk about them in their language. Ten minutes of prep with AI changes the whole conversation.

Prompt
I have a discovery call with a couple in [X] days and want to walk in prepared. The inquiry they sent: [paste it — form, email, anything they said]. My offer and what makes my work distinctive: [paste a paragraph or two about your style, process, and signature elements]. Before the call, tell me: (1) what this couple seems to care about most, based on the actual words they used; (2) the three specific things in my work that most directly speak to those priorities — not generic strengths; (3) the language I should use to describe those things, in their terms not mine; (4) one thoughtful question I can ask that shows I actually read what they wrote and helps me understand them better. Don’t guess at things they didn’t say — if their inquiry is thin, tell me what’s missing instead of inventing it.
No. 07

a referral and repeat-client touchpoint sequence

The clients you’ve already worked with are the warmest leads you’ll ever have, and most of us do nothing with them after the gallery is delivered. A handful of well-timed touchpoints — six months out, a year, an anniversary — quietly compound into referrals and second bookings (engagement to wedding, anniversary portraits, family sessions, vow renewals).

Prompt
Draft a referral and repeat-client touchpoint sequence for my business so I stay in genuine relationship with past clients without being salesy. My voice document: [paste your brand voice document from entry 02]. My service is: [wedding photography / planning / etc.]. Write five touchpoints in order: (1) a thank-you note for the week after gallery/final delivery; (2) a check-in at three months that gives them something useful, not a sales pitch; (3) a six-month touchpoint that offers real value (a print credit, a styling tip, a favorite vendor I think they’d love); (4) a one-year anniversary message; (5) a soft prompt at year two for whatever the natural next session would be (anniversary portraits, family session, vow renewal). For each one, give me the email subject line and the body. Each should feel like a friend, not a marketing automation. No emoji unless they’re in my voice document.
No. 08

pitch language for publications and partnerships

The reason most pitches go unanswered isn’t the work — it’s the pitch. Editors read hundreds. Yours has to be specific, brief, and easy to say yes to.

Prompt
Draft a submission email to [publication] for [the wedding or shoot I’m submitting]. Details about the wedding: [date, location, key vendors, what made it editorially distinctive — not the couple’s love story, but the visual, cultural, or design elements that would interest an editor]. Structure the email as: (1) a one-line subject that names the most editorial hook; (2) opening line that leads with that hook, not a greeting or backstory; (3) two to three sentences on what makes this wedding worth featuring for their specific audience; (4) a one-line vendor credit list with the planner and venue named first; (5) a gallery link; (6) a low-friction close (offering more images, a write-up, a quick call). Total length: under 150 words. Match [publication]’s actual editorial voice based on a recent feature you can reference. Skip everything that sounds like a press release.
No. 09

vendor introduction emails that get answered

Cold outreach to planners, venues, and other creatives is one of the highest-leverage things you can do — and one of the most awkward.

Prompt
Draft a brief introduction email to [planner / venue / florist] at [company]. Specific things I admire about their work: [name two or three concrete details — a recent project, a signature style choice, a value they’ve articulated publicly]. My intent: I’m not pitching for a referral. I’m building real relationships with thoughtful people in [region]. Structure the email as: a warm one-line opener that names something specific (not “I’ve admired your work for a while”); two sentences on why I’m reaching out now; a low-pressure invitation (coffee, a styled shoot collaboration, sending a print I think they’d genuinely enjoy); a soft sign-off. Total length: under 120 words. It must not read as transactional or as if I’m angling for anything.
No. 10

SEO that finds the right couples

You don’t need to become a marketer. You just need your work to be findable by the right people in your region.

Prompt
I’m a [role] in [region] specializing in [style/client type], and my ideal client is [describe in one sentence with budget if relevant]. First, list the 20 search phrases this ideal client would actually type into Google when looking for someone like me — group them as: (a) obvious phrases everyone in my field competes for, (b) specific regional or venue-based phrases with less competition, (c) intent-based phrases that signal a buyer ready to book, and (d) non-obvious phrases I might not have thought of (style descriptors, planning-stage questions, problem-based searches). Then suggest five blog post topics built around the highest-value phrases from groups (b), (c), and (d) — the ones that would feel natural to write and wouldn’t read as SEO-forced. For each post topic, give me a working title, the target search phrase, and a one-line summary of the angle.
Part Three

pricing & packaging

the questions most of us don’t ask out loud
No. 11

a structural review of your pricing

This is the prompt I’ve used most. Pricing is the thing you can’t see clearly when you’re inside it.

Prompt
I want a structural review of my pricing — not generic advice to raise my prices. My current pricing structure: [paste it in full, including all packages, add-ons, and inclusions]. My numbers: average booking [$X], ideal booking [$Y], events booked last year [X], events I want next year [Y], typical client [describe]. Analyze structurally and tell me, in this order: (1) where clients are leaving money on the table — specific places I’ve under-priced or under-included; (2) where I’m creating decision fatigue with too many options or unclear differences; (3) what’s missing that high-end clients in my market expect to see; (4) what’s present that’s actively cheapening the offer (language, inclusions, package names). Then propose a restructured version — specific package names, prices, and inclusions — with a one-paragraph explanation of the strategic shift.
No. 12

use anchoring to make the package you actually want to sell feel obvious

Most of us build pricing as if clients are reading it linearly. They aren’t. They’re comparing. A single price floats — three prices position. The package in the middle, when it sits between a stripped-back option and a notably elevated one, will outsell the same package offered alone almost every time. This isn’t manipulation; it’s giving people a frame to decide inside.

Prompt
I want to use anchoring to make one specific pricing tier feel like the obvious choice. My current pricing structure: [paste it]. The collection I most want to book: [name it and the price]. Restructure my pricing into three tiers using anchoring principles: (1) a lower-priced entry option that’s intentionally limited — shorter coverage, fewer deliverables, no album credit — so the middle looks generous in comparison; (2) the middle being the collection I want to sell, with the inclusions that make it feel like the right answer for most clients; (3) a premium option priced notably higher with elevated inclusions (a full second day, a film add-on, an album upgrade, a print credit) so the middle looks like the obvious smart choice. Present the three tiers as a side-by-side table with package name, price, what’s included, what’s deliberately excluded, and the implied client this tier is for. Then tell me: (a) where the price gaps need to widen or narrow to make the middle the clear winner; (b) what in my current pricing is accidentally working against the anchor effect; (c) the one-line description for each tier that should appear on my pricing sheet.
No. 13

audit your offer for upsells clients would actually want

The fastest way to raise your average sale isn’t to raise your base price — it’s to add the things clients are already asking for after the booking, and price them well. Most of us are sitting on three or four obvious ones we haven’t named yet.

Prompt
I want to raise my average sale by adding upsells that feel natural and valuable, not nickel-and-dime. My current offer: [paste your packages and inclusions in full]. What clients have asked for after booking that wasn’t already included: [list as much as you can remember — extra hours, second shooter, getting-ready coverage, rehearsal dinner, day-after portraits, prints, albums, USB delivery, sneak-peek turnaround upgrade, anything else]. My average booking: [$X]. My typical client: [describe]. Give me 5–10 upsell items that would feel natural for my clients to add. For each one, tell me: (1) what it is, in one line; (2) who it’s right for — the specific client profile most likely to want it; (3) the price I should charge, anchored as a meaningful upgrade not a small add-on, with reasoning for the number; (4) the one-sentence description for my pricing sheet that makes it sell itself; (5) where in the booking flow to introduce it (inquiry, contract, planning call, week before). Skip anything that feels like an upcharge for something basic clients should already get.
No. 14

an inquiry response template that books

Your first reply to an inquiry sets the temperature for the whole relationship. It should feel personal, fast, and not desperate.

Prompt
I want three inquiry response templates that don’t sound like templates. My voice document: [paste from entry 02]. My service: [describe in one line]. Write three responses: (1) Strong-fit lead I want to book — warm, confident, moves them toward a call without being pushy; (2) Partial-fit lead I’m warm on — open the door, ask one clarifying question, leave room to convert; (3) Poor-fit lead I want to decline gracefully — honest about fit, kind, leaves the relationship intact for referrals. For each: include a subject line, the body (under 200 words), and one clear next step. Use natural transitions and conversational rhythm — not bullet points or numbered lists in the actual email. Tell me which lines I’ll need to customize per inquiry so the template stays usable but never feels copy-pasted.
Part Four

contracts & the legal side

the work most of us put off the longest, and where AI is most immediately useful
No. 15

audit your existing contract for gaps

Most of us are working with a contract we wrote five years ago, or one we borrowed from a friend, or one a planner sent us once. AI will read what you have and tell you what’s missing — without you needing to know what you don’t know.

Prompt
I’m a [your role] in [your state] and want a thorough audit of my current client agreement. My contract: [paste in full or attach]. The kind of work it covers: [weddings, portraits, events, etc.]. Read it carefully and tell me, in this order: (1) protective clauses that are missing for my type of work and state — rescheduling, force majeure, model release, image rights, late payment, AI training opt-out, etc.; (2) language that’s vague or could be exploited by a difficult client; (3) anything outdated for how the wedding industry actually works in 2026; (4) anything that reads as overly aggressive or distrustful in a way that could hurt bookings. Then give me the top five issues ranked by risk, and for each one, write the specific replacement clause I should use, in plain language a client would actually read. Note: you’re not a lawyer and I’ll have a real attorney review the final — this is a structural audit to bring to that conversation.
No. 16

build agreements for every kind of work you take on

If you only have one contract, you’re either over-protecting small jobs or under-protecting big ones. I now have separate agreements for weddings, portraits, and non-wedding events — and they took an afternoon to build because I started from one I trusted.

For the rendered, brand-matched PDF, you’ll want the paid tier.

Prompt
I want to build a new agreement variant from my existing contract so I have proper paperwork for every kind of work I take on. My existing contract (the structural and stylistic reference): [paste in full]. The new agreement is for: [portrait session / corporate event / engagement / brand shoot / etc.]. Differences from a wedding: [list anything specific — shorter timeline, different deliverables, different rescheduling expectations, smaller scope, different liability profile]. Draft the new agreement matching my voice, formatting, and clause numbering exactly, with these specific changes: (1) adjust the rescheduling window to [your preference]; (2) modify the deliverables section for this type of work; (3) update the payment schedule if appropriate; (4) flag any clauses from the original that don’t apply to this context, and either remove them or reword them. At the end, list every clause you changed and why so I can review the differences before signing. Note: you’re not a lawyer; I’ll have an attorney review.
No. 17

a working agreement for second shooters and assistants

If you bring on freelancers — second photographers, day-of assistants, associate planners, freelance designers — you need them on paper. This protects your image rights, your client relationships, and your insurance.

Prompt
Draft an independent contractor agreement for a [second photographer / assistant / freelance planner / associate] working under my business. My business is: [describe]. The role: [describe what they’ll do, when, and how often]. Required clauses, in order: (1) scope of work and what counts as a deliverable; (2) image and content ownership — everything they capture or create on my jobs belongs to me; (3) non-solicitation covering my clients and vendor partners for 24 months after the engagement ends; (4) confidentiality covering client information, my pricing, and my internal processes; (5) on-site behavior and dress expectations; (6) payment terms (rate, when paid, what triggers payment); (7) a narrow non-compete limited to direct solicitation of clients I’ve already booked — not a blanket bar on working in my market; (8) a clean termination clause for both parties. Tone: professional but warm. These are colleagues, not adversaries. At the end, flag any clause that might be unenforceable in my state [name your state] so I know what to discuss with my attorney.
No. 18

translate clauses into plain english for clients

When a client asks “what does this part actually mean,” you don’t have to fumble. Paste the clause in and ask AI to explain it in plain language you can copy into an email.

Prompt
A client just asked me to clarify a contract clause. The clause they’re asking about: [paste the exact clause]. What they wrote to me: [paste their question or concern]. Write a short, warm email response that: (1) acknowledges their question without being defensive; (2) explains in plain English what the clause actually means in practice; (3) explains why it’s there — what risk or scenario it covers; (4) clarifies what it does NOT cover, so they don’t over-worry; (5) closes with an open invitation to ask anything else. Keep it under 200 words, no jargon, no legalese. Reassuring but not condescending. Match my voice [paste voice document from entry 02].
Part Five

the day-to-day work

the smaller prompts, used often, that make a week twenty percent lighter
No. 19

audit your post-event workflow for time you’re losing

Most of us have built our post-event process by accretion — one step added at a time, never reviewed as a whole. There are hours hiding in there. AI is exceptionally good at looking at a full process and telling you which steps could be batched, automated, removed, or done in a different order.

Prompt
I want to audit my post-event workflow to find hours I’m losing. Every step I take between the wedding day and final gallery delivery, including the small ones: [list everything — backing up files, culling, editing, sneak peek, blog post, gallery upload, client email, vendor email, social posting, archive, anything else]. For each step, tell me how long it takes: [include rough time per step]. My typical wedding turnaround goal: [X weeks]. Audit the whole process and tell me, in this order: (1) which steps can be batched together to save context-switching time; (2) which can happen in a different order to compress the timeline; (3) which can be templated or automated outright; (4) which can be cut entirely without the client noticing; (5) which I’m under-investing in that would actually elevate the client experience and justify a higher price. End with a single “ideal workflow” outline — the version of this process I should be running — with realistic time estimates per step. Flag any tools or systems I’d need to make this real, and don’t suggest anything that requires me to become a different kind of person to use it.
No. 20

a read on a difficult email before you send it

Before you send the email about the late payment, the rescheduling fee, or the unhappy gallery review — let AI pressure-test it.

Prompt
I want a pressure-test on a difficult email before I send it. The situation: [describe what happened, what’s at stake, what I want the outcome to be]. The email I’m thinking of sending: [paste it in full, including subject line]. My voice document for reference: [paste from entry 02]. Read the email as if you were the client receiving it on a Tuesday morning, then tell me: (1) where it lands wrong — specific lines that read defensive, cold, passive-aggressive, or transactional; (2) where I’m protecting myself at the expense of the relationship; (3) where I’m being too soft and risk being walked over; (4) what the client is most likely to do or feel after reading it. Then rewrite it to be firm but warm — clear about the boundary or ask, but human. Keep my voice. Show me both versions side by side so I can see what changed.
No. 21

vendor spec sheets and shot lists, customized per event

Every event is different. Your prep documents should be too — but they shouldn’t take an hour to build.

Prompt
Build a [photographer prep sheet / day-of timeline / family portrait list] for an upcoming [wedding / event]. The details: [paste the timeline, vendor list, ceremony and reception locations, key family members and any sensitivity, expected guest count, anything unusual about the day]. My typical coverage approach: [describe in one line]. Format the document for printing on a single page if possible. Use clear section headers, no jargon, and keep the language warm enough that I could share it with a planner or assistant. Then flag, separately, anything in the timeline that looks unrealistic or under-buffered — specific moments where I’ll run out of time, where transitions are too tight, or where one delay will cascade through the rest of the day. For each flagged item, suggest the buffer it should have.
No. 22

blog posts that actually get written

Most of us don’t blog because we don’t have time to write 1,500 words. AI can do the structural work; you do the voice.

Prompt
Help me structure a blog post from rough notes. The topic: [a recent wedding / venue review / piece of advice / behind-the-scenes story]. My notes: [paste everything you have, even if it’s messy]. My voice document: [paste from entry 02]. Who this is for: [describe the reader — engaged couples in [region], industry peers, past clients]. Structure my notes into a 600–900 word post with: (1) an opening line that isn’t “every wedding is special” or any other cliché; (2) three or four section breaks where I can paste images, with one-line section headers; (3) a closing that gives the reader something useful to take with them — a question, a takeaway, an honest observation; (4) SEO-friendly title options (3 to choose from), a meta description under 155 characters, and the target search phrase. Match my voice exactly. Skip anything that sounds like a wedding-blog template.
Part Six

how to actually talk to AI

a few small habits that make every prompt above work better
No. 23

set the terms before you start

The most important sentence you can put at the top of any conversation with AI is the one that tells it how to behave. Used well, it isn’t the AI’s judgment shaping your business — it’s your judgment, scaled. Make it explicit. Tell it to be honest, to push back when something seems off, to never invent facts or names or statistics, and to flag anything that could land as hurtful, discriminatory, or careless. Then hold it to that standard the same way you’d hold a thoughtful colleague.

This is also a quiet reminder for ourselves. The work we do is built on real relationships with real people on some of the most meaningful days of their lives. AI should help us serve them better, not faster at their expense.

Prompt
Before we start, here’s how I’d like you to work with me throughout this conversation: be honest, even when it’s uncomfortable. Tell me when you don’t know something instead of inventing it — never make up names, statistics, quotes, or sources. Push back on me when my thinking is weak or when I’m about to make a mistake. Be kind without being flattering. Flag anything in your draft that could come across as exclusionary, insensitive, or stereotyped — especially around culture, body, gender, family structure, or background. Suggest the more thoughtful alternative. If you’re ever unsure how something might land, ask me before you commit to it on the page.
No. 24

give it your voice before asking it to write in your voice

The single biggest difference between AI-flavored writing and writing that sounds like you is whether you fed it samples first. Three captions. A blog post. An old client email. That’s enough. The brand voice document in entry 02 is the highest-leverage thing you’ll build all year. Once you have it, paste this at the top of any conversation where the writing matters.

Prompt
Before I ask you to write anything, study my voice carefully. My brand voice document: [paste from entry 02]. Plus 5–8 recent pieces of writing I’m proud of: [paste them — captions, emails, blog excerpts, anything]. Now tell me, in three sentences: what you notice about my sentence rhythm, the words I reach for and avoid, and my emotional register. For everything you draft in this conversation: match what you just identified. If a draft starts to drift toward generic AI rhythm — lists of three, neat parallel structures, soft hedges, vague intensifiers — flag it before showing me. If I push back and say “this doesn’t sound like me,” come back to this message and recalibrate.
No. 25

push back when the answer isn’t useful

If AI gives you a generic answer, tell it. “That’s too generic — be more specific.” “That sounds like AI — rewrite without the rhythm of three.” “Cut the praise and just answer the question.” It will get better. The first answer is rarely the best one, and you don’t have to start over to get a better one. It’s not rude, either. It’s how a working colleague would talk to another working colleague.

No. 26

treat it like a sharp colleague, not an oracle

Don’t ask “what should I do.” Ask “here’s what I’m thinking — what am I missing.” The tool is good. Your judgment is better. The work happens at the intersection. And nobody — not me, not Claude, not anyone — knows your business the way you do.

If something in here helped, I’d love to hear about it. Find me on Instagram, send me an email, write back. The best version of this guide is the one shaped by the people actually using it.

carlie@carliestatsky.com

First Edition · 2026